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Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams.

Angewandte Chemie (International ed. in English)

Goudedranche S, Besnard C, Egger L, Lacour J.
PMID: 27701808
Angew Chem Int Ed Engl. 2016 Oct 24;55(44):13775-13779. doi: 10.1002/anie.201607574. Epub 2016 Oct 04.

N-aryl γ-lactams react intermolecularly with acceptor-acceptor diazo reagents, usually dicarbonyl compounds, in a copper-catalyzed process to yield functionalized pyrrolidines with α-pseudoquaternary centers. As 1,2-acyl or -phosphoryl migration is preferred, single regioisomers are obtained. Furthermore, in the presence of a...

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Goudedranche S, Besnard C, Egger L, et al. Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams. Angew Chem Int Ed Engl. 2016;55(44):13775-13779doi: 10.1002/anie.201607574.
Goudedranche, S., Besnard, C., Egger, L., & Lacour, J. (2016). Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams. Angewandte Chemie (International ed. in English), 55(44), 13775-13779. https://doi.org/10.1002/anie.201607574
Goudedranche, Sébastien, et al. "Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams." Angewandte Chemie (International ed. in English) vol. 55,44 (2016): 13775-13779. doi: https://doi.org/10.1002/anie.201607574
Goudedranche S, Besnard C, Egger L, Lacour J. Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams. Angew Chem Int Ed Engl. 2016 Oct 24;55(44):13775-13779. doi: 10.1002/anie.201607574. Epub 2016 Oct 04. PMID: 27701808.
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Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines.

Organic & biomolecular chemistry

Zhao BL, Lin Y, Yan HH, Du DM.
PMID: 26426388
Org Biomol Chem. 2015 Dec 14;13(46):11351-61. doi: 10.1039/c5ob01749a.

A bifunctional squaramide catalysed aza-Michael/Michael cascade reaction between nitroalkenes and tosylaminomethyl enones or enoates has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chiral pyrrolidines with a broad substrate scope, giving the desired products in...

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Zhao BL, Lin Y, Yan HH, et al. Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines. Org Biomol Chem. 2015;13(46):11351-61doi: 10.1039/c5ob01749a.
Zhao, B. L., Lin, Y., Yan, H. H., & Du, D. M. (2015). Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines. Organic & biomolecular chemistry, 13(46), 11351-61. https://doi.org/10.1039/c5ob01749a
Zhao, Bo-Liang, et al. "Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines." Organic & biomolecular chemistry vol. 13,46 (2015): 11351-61. doi: https://doi.org/10.1039/c5ob01749a
Zhao BL, Lin Y, Yan HH, Du DM. Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines. Org Biomol Chem. 2015 Dec 14;13(46):11351-61. doi: 10.1039/c5ob01749a. PMID: 26426388.
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Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide.

Angewandte Chemie (International ed. in English)

Grünenfelder CE, Kisunzu JK, Wennemers H.
PMID: 27254460
Angew Chem Int Ed Engl. 2016 Jul 18;55(30):8571-4. doi: 10.1002/anie.201602230. Epub 2016 Jun 02.

The tripeptide H-dPro-Pro-Asn-NH2 is presented as a catalyst for asymmetric conjugate addition reactions of aldehydes to maleimide. The peptidic catalyst promotes the reaction between various aldehydes and unprotected maleimide with high stereoselectivities and yields. The obtained products were readily...

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Grünenfelder CE, Kisunzu JK, Wennemers H. Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide. Angew Chem Int Ed Engl. 2016;55(30):8571-4doi: 10.1002/anie.201602230.
Grünenfelder, C. E., Kisunzu, J. K., & Wennemers, H. (2016). Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide. Angewandte Chemie (International ed. in English), 55(30), 8571-4. https://doi.org/10.1002/anie.201602230
Grünenfelder, Claudio E, et al. "Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide." Angewandte Chemie (International ed. in English) vol. 55,30 (2016): 8571-4. doi: https://doi.org/10.1002/anie.201602230
Grünenfelder CE, Kisunzu JK, Wennemers H. Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide. Angew Chem Int Ed Engl. 2016 Jul 18;55(30):8571-4. doi: 10.1002/anie.201602230. Epub 2016 Jun 02. PMID: 27254460.
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Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines.

Chemical science

Turnpenny BW, Chemler SR.
PMID: 24932404
Chem Sci. 2014 May 01;5(5):1786-1793. doi: 10.1039/C4SC00237G.

Chiral vicinal diamines, including 2-aminomethyl indolines and pyrrolidines, are useful as ligands for catalytic asymmetric reactions and are also found as important components of bioactive compounds. Herein is reported the first copper-catalyzed alkene diamination that occurs with high enantioselectivity....

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Turnpenny BW, Chemler SR. Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines. Chem Sci. 2014;5(5):1786-1793doi: 10.1039/C4SC00237G.
Turnpenny, B. W., & Chemler, S. R. (2014). Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines. Chemical science, 5(5), 1786-1793. https://doi.org/10.1039/C4SC00237G
Turnpenny, Benjamin W, and Chemler, Sherry R. "Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines." Chemical science vol. 5,5 (2014): 1786-1793. doi: https://doi.org/10.1039/C4SC00237G
Turnpenny BW, Chemler SR. Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines. Chem Sci. 2014 May 01;5(5):1786-1793. doi: 10.1039/C4SC00237G. PMID: 24932404; PMCID: PMC4051238.
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Gold-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters to cis-cyclohepta-4,8-diene-fused pyrrolidines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Rao W, Sally, Berry SN, Chan PW.
PMID: 25113644
Chemistry. 2014 Oct 06;20(41):13174-80. doi: 10.1002/chem.201402500. Epub 2014 Aug 11.

A synthetic approach that provides access to cis-cyclohepta-4,8-diene-fused pyrrolidines efficiently through Au(I) -catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters at a low catalyst loading of 2 mol % is reported. Starting carbonates and esters with a pendant alkyl group...

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Rao W, Sally, Berry SN, et al. Gold-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters to cis-cyclohepta-4,8-diene-fused pyrrolidines. Chemistry. 2014;20(41):13174-80doi: 10.1002/chem.201402500.
Rao, W., Sally, Berry, S. N., & Chan, P. W. (2014). Gold-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters to cis-cyclohepta-4,8-diene-fused pyrrolidines. Chemistry (Weinheim an der Bergstrasse, Germany), 20(41), 13174-80. https://doi.org/10.1002/chem.201402500
Rao, Weidong, et al. "Gold-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters to cis-cyclohepta-4,8-diene-fused pyrrolidines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,41 (2014): 13174-80. doi: https://doi.org/10.1002/chem.201402500
Rao W, Sally, Berry SN, Chan PW. Gold-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters to cis-cyclohepta-4,8-diene-fused pyrrolidines. Chemistry. 2014 Oct 06;20(41):13174-80. doi: 10.1002/chem.201402500. Epub 2014 Aug 11. PMID: 25113644.
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Ag2CO3/CA-AA-AmidPhos Multifunctional Catalysis in the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides.

Organic letters

Wang H, Deng Q, Zhou Z, Hu S, Liu Z, Zhou LY.
PMID: 26745747
Org Lett. 2016 Feb 05;18(3):404-7. doi: 10.1021/acs.orglett.5b03430. Epub 2016 Jan 08.

The new Ag2CO3/CA-AA-amidphos complexes have been demonstrated as highly efficient multifunctional catalysts in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. Under optimal conditions, highly functionalized endo-4 pyrrolidines were obtained with excellent yields (up to 99% yield) and enantioselectivities (up...

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Wang H, Deng Q, Zhou Z, et al. Ag2CO3/CA-AA-AmidPhos Multifunctional Catalysis in the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides. Org Lett. 2016;18(3):404-7doi: 10.1021/acs.orglett.5b03430.
Wang, H., Deng, Q., Zhou, Z., Hu, S., Liu, Z., & Zhou, L. Y. (2016). Ag2CO3/CA-AA-AmidPhos Multifunctional Catalysis in the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides. Organic letters, 18(3), 404-7. https://doi.org/10.1021/acs.orglett.5b03430
Wang, Haifei, et al. "Ag2CO3/CA-AA-AmidPhos Multifunctional Catalysis in the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides." Organic letters vol. 18,3 (2016): 404-7. doi: https://doi.org/10.1021/acs.orglett.5b03430
Wang H, Deng Q, Zhou Z, Hu S, Liu Z, Zhou LY. Ag2CO3/CA-AA-AmidPhos Multifunctional Catalysis in the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides. Org Lett. 2016 Feb 05;18(3):404-7. doi: 10.1021/acs.orglett.5b03430. Epub 2016 Jan 08. PMID: 26745747.
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Ligand-Controlled Divergent C-H Functionalization of Aldehydes with Enynes by Cobalt Catalysts.

Journal of the American Chemical Society

Santhoshkumar R, Mannathan S, Cheng CH.
PMID: 26645104
J Am Chem Soc. 2015 Dec 30;137(51):16116-20. doi: 10.1021/jacs.5b10447. Epub 2015 Dec 16.

We describe a highly step and atom economical cobalt-catalyzed cyclization of 1,6-enynes with aldehydes to synthesize functionalized pyrrolidines and dihydrofurans with high chemo- and stereoselectivity. The catalytic reaction plausibly proceeds via the cobaltacycle intermediate generated from the reaction of...

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Santhoshkumar R, Mannathan S, Cheng CH. Ligand-Controlled Divergent C-H Functionalization of Aldehydes with Enynes by Cobalt Catalysts. J Am Chem Soc. 2015;137(51):16116-20doi: 10.1021/jacs.5b10447.
Santhoshkumar, R., Mannathan, S., & Cheng, C. H. (2015). Ligand-Controlled Divergent C-H Functionalization of Aldehydes with Enynes by Cobalt Catalysts. Journal of the American Chemical Society, 137(51), 16116-20. https://doi.org/10.1021/jacs.5b10447
Santhoshkumar, Rajagopal, et al. "Ligand-Controlled Divergent C-H Functionalization of Aldehydes with Enynes by Cobalt Catalysts." Journal of the American Chemical Society vol. 137,51 (2015): 16116-20. doi: https://doi.org/10.1021/jacs.5b10447
Santhoshkumar R, Mannathan S, Cheng CH. Ligand-Controlled Divergent C-H Functionalization of Aldehydes with Enynes by Cobalt Catalysts. J Am Chem Soc. 2015 Dec 30;137(51):16116-20. doi: 10.1021/jacs.5b10447. Epub 2015 Dec 16. PMID: 26645104.
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Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines.

Organic letters

Cheng YF, Rong HJ, Yi CB, Yao JJ, Qu J.
PMID: 26378343
Org Lett. 2015 Oct 02;17(19):4758-61. doi: 10.1021/acs.orglett.5b02298.

By using o-benzoquinone as an internal oxidant, the regio- and diastereoselective functionalization of the secondary over the tertiary α-C-H bond of 2-substituted pyrrolidines is first realized. Subsequent intermolecular addition of a nucleophile to the generated N,O-acetal and cleavage of...

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Cheng YF, Rong HJ, Yi CB, et al. Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines. Org Lett. 2015;17(19):4758-61doi: 10.1021/acs.orglett.5b02298.
Cheng, Y. F., Rong, H. J., Yi, C. B., Yao, J. J., & Qu, J. (2015). Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines. Organic letters, 17(19), 4758-61. https://doi.org/10.1021/acs.orglett.5b02298
Cheng, Yong-Feng, et al. "Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines." Organic letters vol. 17,19 (2015): 4758-61. doi: https://doi.org/10.1021/acs.orglett.5b02298
Cheng YF, Rong HJ, Yi CB, Yao JJ, Qu J. Redox-Triggered α-C-H Functionalization of Pyrrolidines: Synthesis of Unsymmetrically 2,5-Disubstituted Pyrrolidines. Org Lett. 2015 Oct 02;17(19):4758-61. doi: 10.1021/acs.orglett.5b02298. PMID: 26378343.
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Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation.

European journal of organic chemistry

Rackl D, Kais V, Lutsker E, Reiser AO.
PMID: 28529446
European J Org Chem. 2017 Apr 18;2017(15):2130-2138. doi: 10.1002/ejoc.201700014. Epub 2017 Feb 28.

The synthesis of chiral tetrahydrofurans and pyrrolidines starting from 1,2-diols or β-amino alcohols, respectively, by visible-light-mediated deoxygenation is described. Easily accessible monoallylated/propargylated substrates were activated either as inexpensive ethyl oxalates or as recyclable 3,5-bis(trifluoromethyl)benzoates to generate alkyl radicals suitable...

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Rackl D, Kais V, Lutsker E, et al. Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation. European J Org Chem. 2017;2017(15):2130-2138doi: 10.1002/ejoc.201700014.
Rackl, D., Kais, V., Lutsker, E., & Reiser, A. O. (2017). Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation. European journal of organic chemistry, 2017(15), 2130-2138. https://doi.org/10.1002/ejoc.201700014
Rackl, Daniel, et al. "Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation." European journal of organic chemistry vol. 2017,15 (2017): 2130-2138. doi: https://doi.org/10.1002/ejoc.201700014
Rackl D, Kais V, Lutsker E, Reiser AO. Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation. European J Org Chem. 2017 Apr 18;2017(15):2130-2138. doi: 10.1002/ejoc.201700014. Epub 2017 Feb 28. PMID: 28529446; PMCID: PMC5412674.
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Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Feraldi-Xypolia A, Gomez Pardo D, Cossy J.
PMID: 26218227
Chemistry. 2015 Sep 07;21(37):12876-80. doi: 10.1002/chem.201502084. Epub 2015 Jul 23.

A ring contraction of 3-hydroxy-3-(trifluoromethyl)piperidines was achieved via an aziridinium intermediate. This contraction facilitates the synthesis of a series of 2-substituted 2-(trifluoromethyl)pyrrolidines incorporating a quaternary center at the C2 position.

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Feraldi-Xypolia A, Gomez Pardo D, Cossy J. Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry. 2015;21(37):12876-80doi: 10.1002/chem.201502084.
Feraldi-Xypolia, A., Gomez Pardo, D., & Cossy, J. (2015). Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry (Weinheim an der Bergstrasse, Germany), 21(37), 12876-80. https://doi.org/10.1002/chem.201502084
Feraldi-Xypolia, Alexandra, et al. "Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,37 (2015): 12876-80. doi: https://doi.org/10.1002/chem.201502084
Feraldi-Xypolia A, Gomez Pardo D, Cossy J. Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry. 2015 Sep 07;21(37):12876-80. doi: 10.1002/chem.201502084. Epub 2015 Jul 23. PMID: 26218227.
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Direct Asymmetric Aza-Vinylogous-Type Michael Additions of Nitrones from Isatins to Nitroalkenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Zhan G, Shi ML, Lin WJ, Ouyang Q, Du W, Chen YC.
PMID: 28337796
Chemistry. 2017 May 05;23(26):6286-6289. doi: 10.1002/chem.201701290. Epub 2017 Apr 19.

Nitrones commonly act as 1,3-dipoles and electrophiles to furnish valuable isoxazolidine and N-hydroxyl products, respectively. They also can be converted to nitrone ylide species and undergo [3+2] formal cycloadditions to access N-hydroxyl pyrrolidines. Here, asymmetric direct aza-vinylogous-type additions of...

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Zhan G, Shi ML, Lin WJ, et al. Direct Asymmetric Aza-Vinylogous-Type Michael Additions of Nitrones from Isatins to Nitroalkenes. Chemistry. 2017;23(26):6286-6289doi: 10.1002/chem.201701290.
Zhan, G., Shi, M. L., Lin, W. J., Ouyang, Q., Du, W., & Chen, Y. C. (2017). Direct Asymmetric Aza-Vinylogous-Type Michael Additions of Nitrones from Isatins to Nitroalkenes. Chemistry (Weinheim an der Bergstrasse, Germany), 23(26), 6286-6289. https://doi.org/10.1002/chem.201701290
Zhan, Gu, et al. "Direct Asymmetric Aza-Vinylogous-Type Michael Additions of Nitrones from Isatins to Nitroalkenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,26 (2017): 6286-6289. doi: https://doi.org/10.1002/chem.201701290
Zhan G, Shi ML, Lin WJ, Ouyang Q, Du W, Chen YC. Direct Asymmetric Aza-Vinylogous-Type Michael Additions of Nitrones from Isatins to Nitroalkenes. Chemistry. 2017 May 05;23(26):6286-6289. doi: 10.1002/chem.201701290. Epub 2017 Apr 19. PMID: 28337796.
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Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides.

Organic & biomolecular chemistry

Muthusamy S, Kumar SG.
PMID: 26786749
Org Biomol Chem. 2016 Feb 21;14(7):2228-40. doi: 10.1039/c5ob02322j. Epub 2016 Jan 20.

Investigations of regio-, chemo- and diastereoselective studies on three- as well as four-component reactions using diazooxindoles, imines, aldehydes, amines, alkenes, alkynes or diazenes in the presence of copper(I) thiophene-2-carboxylate are performed to furnish spiroindolo-pyrrolidine/-imidazolidine/-triazolidine ring systems in good yields....

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Muthusamy S, Kumar SG. Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides. Org Biomol Chem. 2016;14(7):2228-40doi: 10.1039/c5ob02322j.
Muthusamy, S., & Kumar, S. G. (2016). Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides. Organic & biomolecular chemistry, 14(7), 2228-40. https://doi.org/10.1039/c5ob02322j
Muthusamy, Sengodagounder, and Kumar, Singaravelan Ganesh. "Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides." Organic & biomolecular chemistry vol. 14,7 (2016): 2228-40. doi: https://doi.org/10.1039/c5ob02322j
Muthusamy S, Kumar SG. Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides. Org Biomol Chem. 2016 Feb 21;14(7):2228-40. doi: 10.1039/c5ob02322j. Epub 2016 Jan 20. PMID: 26786749.
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